pazopanib   

GtoPdb Ligand ID: 5698

Synonyms: GW 786034 | indazolylpyrimidine 13 [4] | Votrient®
pazopanib is an approved drug (FDA (2009), EMA (2010))
Compound class: Synthetic organic
Comment: Pazopanib is a Type-1 kinase inhibitor. Its discovery is reported in [5]. It targets multiple receptor tyrosine kinases (VEGFR1, VEGFR2, VEGFR3, PDGFRβ, FGFR1, Kit and CSF1R).
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 5
Topological polar surface area 127.41
Molecular weight 437.16
XLogP 3.34
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CN(c1ccc2c(c1)nn(c2C)C)c1ccnc(n1)Nc1ccc(c(c1)S(=O)(=O)N)C
Isomeric SMILES CN(c1ccc2c(c1)nn(c2C)C)c1ccnc(n1)Nc1ccc(c(c1)S(=O)(=O)N)C
InChI InChI=1S/C21H23N7O2S/c1-13-5-6-15(11-19(13)31(22,29)30)24-21-23-10-9-20(25-21)27(3)16-7-8-17-14(2)28(4)26-18(17)12-16/h5-12H,1-4H3,(H2,22,29,30)(H,23,24,25)
InChI Key CUIHSIWYWATEQL-UHFFFAOYSA-N
References
1. Anastassiadis T, Deacon SW, Devarajan K, Ma H, Peterson JR. (2011)
Comprehensive assay of kinase catalytic activity reveals features of kinase inhibitor selectivity.
Nat. Biotechnol., 29 (11): 1039-45. [PMID:22037377]
2. Davis MI, Hunt JP, Herrgard S, Ciceri P, Wodicka LM, Pallares G, Hocker M, Treiber DK, Zarrinkar PP. (2011)
Comprehensive analysis of kinase inhibitor selectivity.
Nat. Biotechnol., 29 (11): 1046-51. [PMID:22037378]
3. Gao Y, Davies SP, Augustin M, Woodward A, Patel UA, Kovelman R, Harvey KJ. (2013)
A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery.
Biochem. J., 451 (2): 313-28. [PMID:23398362]
4. Harris PA, Boloor A, Cheung M, Kumar R, Crosby RM, Davis-Ward RG, Epperly AH, Hinkle KW, Hunter 3rd RN, Johnson JH et al.. (2008)
Discovery of 5-[[4-[(2,3-dimethyl-2H-indazol-6-yl)methylamino]-2-pyrimidinyl]amino]-2-methyl-benzenesulfonamide (Pazopanib), a novel and potent vascular endothelial growth factor receptor inhibitor.
J. Med. Chem., 51 (15): 4632-40. [PMID:18620382]
5. Harris PA, Cheung M, Hunter 3rd RN, Brown ML, Veal JM, Nolte RT, Wang L, Liu W, Crosby RM, Johnson JH et al.. (2005)
Discovery and evaluation of 2-anilino-5-aryloxazoles as a novel class of VEGFR2 kinase inhibitors.
J. Med. Chem., 48 (5): 1610-9. [PMID:15743202]
6. Wodicka LM, Ciceri P, Davis MI, Hunt JP, Floyd M, Salerno S, Hua XH, Ford JM, Armstrong RC, Zarrinkar PP et al.. (2010)
Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry.
Chem. Biol., 17 (11): 1241-9. [PMID:21095574]